Old Navy Denim Haul: My New Favorite Skinny Jeans

There are a few places that just feel like a guaranteed good time for me, and Old Navy is definitely one of them. The second I walk in, I can already picture new outfits in my head. And if you know anything about me and Aisha’s Fashion Faves, you know I have a soft spot for their denim section. So when I heard they were having a big sale on denim, tops, shoes, and even undergarments, I grabbed my tote, put on some lip gloss, and headed straight to my neighborhood Old Navy here in Chicago.

Heading Straight for the Denim Wall

Whenever I walk into Old Navy, I make a beeline for the denim wall. It’s my happy place: row after row of jeans in every rise, wash, and fit you can imagine. That day, the store felt extra buzzy. You could tell everyone had heard about the sale, and people were loading up their arms with jeans and cozy tops. I took a deep breath, reminded myself to stay focused, and dove into the denim section, which is hands-down my favorite spot in the whole store.

I started scanning the stacks, running my hand over different washes, checking out the labels for anything new I hadn’t tried yet. Almost immediately, two styles jumped out at me: the WOW Skinny denim and the Rockstar Skinny denim. I’d worn Rockstar before and loved them, but WOW Skinny was new to me, and you know I can’t resist trying a fresh fit.

The best part? Both styles were on sale. No complicated math, no stressing over price tags — just the quiet joy of knowing this was the perfect day to stock up. I ended up grabbing two pairs of Rockstar Skinny denim and two pairs of WOW Skinny denim in different washes so I could really play around with styling.

Tops to Match: Building Easy Everyday Outfits

Once my arms were full of denim, I wandered over to the tops. I wanted pieces that felt like “me” but would also work hard in my wardrobe — the kind of tops you can throw on half-asleep on a Monday morning and still look pulled together.

I found a soft, slightly oversized striped tee that felt very “weekend coffee run” and a simple, fitted black tee that I knew would be perfect for dressing up or down. Both had that relaxed Old Navy vibe but still looked polished enough for real life: brunch with friends, errands around the city, or even casual Fridays in the office.

With two tops and four pairs of jeans in hand, I headed to the fitting room for my favorite part of any shopping trip: the try-on session.

WOW Skinny Denim: Comfy, Stretchy, and City-Ready

I started with the WOW Skinny denim because I was the most curious about them. The first pair I tried was a classic medium wash — that sweet spot between dressy and casual. When I pulled them on, the first thing I noticed was the stretch. These jeans have that “move with you” feel that makes them perfect for a full day of Chicago living, from hopping on the train to walking several blocks in unpredictable weather.

The rise hit me comfortably around the mid- to high-rise range, which I love because it gives a little support around the midsection without feeling restrictive. They smoothed everything out but still let me breathe, sit, and, yes, do a little fitting room dance to check the booty situation. Approved.

With the striped tee tucked in at the front and some white sneakers I’d worn to the store, the WOW Skinny jeans gave me that effortless, off-duty vibe. I could see them working for Saturday markets, grabbing coffee in Logan Square, or just running errands on a busy weekday. I also tried them with the black fitted tee, half-tucked, and suddenly the look shifted to “casual dinner” or “drinks with friends” with just a quick shoe change to ankle boots or strappy sandals.

The second pair of WOW Skinny denim I tried was a darker wash, which instantly felt a little dressier. Same comfy stretch, same flattering rise, but with that sleek, put-together finish that makes them perfect for those days when you have no time to think but still want to look intentional. These are the jeans I’ll reach for when I’m going from the office straight to a casual evening out.

Rockstar Skinny Denim: A Tried-and-True Favorite

Next up were the Rockstar Skinny jeans — an Old Navy classic that I keep coming back to. I slipped into the first pair, a slightly faded blue wash, and immediately remembered why they’re so popular. The fit is snug in all the right places but doesn’t feel like a denim corset. There’s enough stretch to move comfortably, but the fabric still feels like real jeans, not leggings pretending to be denim.

The rise sat just where I like it: high enough to pair with crop-ish tops or do a full tuck without worrying about anything slipping or gapping, but not so high that it hits my ribcage. For everyday Chicago life — think walking to the train, sitting at a desk, climbing stairs, and dodging puddles when the weather acts up — the Rockstar Skinny fit feels dependable and secure.

Styled with the black fitted tee tucked in completely, the faded Rockstar wash gave me that classic jeans-and-a-tee look that never fails. Add a leather jacket and some heeled booties, and suddenly it’s a full-on “date night but still comfortable” outfit.

The second Rockstar pair I tried was a darker rinse, which instantly made my legs look a mile long. I paired them with the striped tee, sleeves pushed up, and imagined them with a trench coat and loafers for those crisp Chicago fall days. These are the jeans I’ll wear when I want to feel polished but still need the practicality of skinnies that tuck easily into boots.

Who Old Navy WOW & Rockstar Skinny Jeans Work Best For

One of the reasons I keep coming back to Old Navy denim is that they really do a great job of fitting a wide range of bodies. For reference, I’m mid-size with curves through my hips and thighs, and both the WOW Skinny and Rockstar Skinny make me feel smoothed, supported, and still able to move like a real person who climbs stairs and hustles for the train.

If you’re curvy through the hip and thigh, the WOW Skinny is such a win. The stretch is really forgiving without bagging out by midday, and the mid- to high-rise helps avoid that dreaded gap in the back when you sit or bend. I’d say stick to your usual Old Navy size if you like a snug, sculpting fit, or go up one if you prefer a little more breathing room or want them to look more like a slim straight from the knee down.

The Rockstar Skinny feels a little more structured on me, which I love for days when I want to feel extra held-in. If you’re mid-size, hourglass, or carry more weight in your midsection, the higher rise is super flattering and great for tucking in tops. Petites might like the Rockstar in the short or petite inseam so you’re not swimming in extra fabric at the ankle, and taller friends can usually grab the long inseam and still get that true skinny-jean look.

For my tall readers, both styles come in multiple inseams, so you don’t have to choose between cold ankles and weird capri lengths. If you’re on the petite side, I’d try the petite or short first and only cuff if you really want that ankle detail. Mid-size friends, I see you: don’t be afraid to grab two sizes and really move around in the fitting room. Old Navy denim is forgiving, but the right size will feel secure without cutting in.

• Fit tip for WOW Skinny: Great if you’re curvy, mid-size, or want comfort for all-day wear. Check the waist for gapping and the knee for bunching when you walk.
• Fit tip for Rockstar Skinny: Perfect if you like a more structured, “held in” feel. Try your usual size first; if you’re between sizes or prefer a relaxed skinny, you can size up and still get a sleek leg.

How I’m Styling My New Denim

By the time I finished trying everything on, I already had a mental lookbook going:

• WOW Skinny (medium wash) + striped tee: Perfect for weekend errands, brunch, or a casual day date. I’ll throw on sneakers or simple slides and maybe add a crossbody bag.
• WOW Skinny (dark wash) + black tee: Easy “desk to dinner” combo. Swap flats for block heels, add a blazer, and I’m good to go.
• Rockstar Skinny (faded blue) + black tee: Classic, everyday uniform. I’ll wear this with a denim jacket or moto jacket and my favorite ankle boots.
• Rockstar Skinny (dark rinse) + striped tee: Slightly more polished casual look, perfect for meetings, casual Fridays, or museum days downtown.

All four pairs feel comfortable enough for full days on my feet, but still fitted and flattering. That balance of stretch and structure is really what makes Old Navy denim such a staple in my closet.

Outfit Ideas by Occasion

If you’re staring at your closet wondering how to actually wear these on real-life days, here are some easy outfit ideas using the exact pieces I grabbed: the WOW Skinny and Rockstar Skinny jeans, plus the striped tee, black fitted tee, and simple sneakers, booties, or sandals you probably already own.

• Brunch with friends: WOW Skinny (medium wash) + striped tee, front-tucked, with white sneakers or simple slides. Add a crossbody bag and sunnies and you’re done.
• Casual Fridays at work: Rockstar Skinny (dark rinse) + black fitted tee fully tucked in. Throw on a blazer or trench and loafers or low block heels. It feels office-appropriate but still comfy enough for after-work drinks.
• Running errands: WOW Skinny (medium or dark wash) + striped tee, sleeves pushed up, with your most comfortable sneakers. If it’s chilly, layer a denim jacket or light puffer on top and you’re ready for grocery runs and Target laps.
• Simple date night: Rockstar Skinny (faded or dark rinse) + black fitted tee tucked in, leather or moto jacket, and heeled booties or strappy sandals. Swap your daytime tote for a smaller bag and maybe add a red lip, and suddenly you’ve got an easy, low-effort date-night look.

My goal with any haul like this is to make sure every piece can pull double or triple duty in my wardrobe. With just two tops, four pairs of jeans, and a few shoe options, I can mix and match my way through brunches, workdays, errands, and date nights without feeling like I’m repeating the exact same outfit.

Tips for Shopping Old Navy Denim Sales

If you’re planning your own Old Navy denim haul soon, here are a few quick tips to help you make the most of those sale days:

• Check the sale racks first: Sometimes the best washes and fits are hiding in the clearance or sale section. Don’t skip it.
• Try different rises: Mid-rise, high-rise, and everything in between can fit totally differently, even in the same size. Grab a few options and see what feels best on your body.
• Play with washes: A medium wash might be your weekend go-to, while a dark wash can double as “dressy denim” for work or nights out.
• Move around in the fitting room: Sit, bend, walk in place. Make sure your jeans feel good in real-life positions, not just when you’re standing still.
• Bring (or wear) your usual shoes: If you love wearing boots, sneakers, or heels, try your jeans with that shoe style to check the length and overall vibe.

Your Turn: Share Your Old Navy Denim Faves

Walking out of Old Navy with my bag full of WOW Skinny and Rockstar Skinny denim felt like such a win. I know these jeans are going to be on heavy rotation in my wardrobe, especially as Chicago weather does its usual mood swings and I need outfits that can keep up.

If you’ve been thinking about refreshing your denim drawer, consider this your sign to check out Old Navy’s denim section, especially when they’re having a sale. And now I want to hear from you: Do you have a favorite Old Navy denim style? Are you team WOW, team Rockstar, or something else entirely? Tell me your Old Navy denim faves in the comments — I love getting new recommendations from you all.